KR840005131A - Process for preparing N-heterocyclosulfonyl-N'-pyriminyl urea and N-heterocyclosulfonyl-N-triazinyl urea - Google Patents

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Process for preparing N-heterocyclosulfonyl-N'-pyriminyl urea and N-heterocyclosulfonyl-N-triazinyl urea

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Claims (14)

a) reacting a heterocyclosulfonamide of formula (II) with N-pyrimidinylcarbamate or N-triazinylcarbamate of formula (III) in the presence thereof, or b) a general formula (IV) a reaction of heterocyclofonyl isocyanate or heterocyclosulfonyl isocyanate with aminopyrimidine or aminotriazine of general formula (V) in the presence of a base, or c) Heterocyclosulfonamide of II) and isocyanate or isothiocyanate of general formula (VI) are reacted in the presence of a base, or d) N-heterocyclosulfonylcarbamate of general formula (VII) and the N-heterocyclosulfonyl-N'-triazinyl urea or N-heterocyclosuccinin-N-triazinyl urea of the following general formula (I) reacted with aminopyrimidine or aminotriazine of general formula (V) Or otitis Article methods. Wherein X is oxygen, sulfur, or And Y and Z are oxygen or sulfur, E is nitrogen or —CH =, R ₁ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C haloalcohol, C _1- C ₄ alkoxy, halogen C ₁ -C ₄ alkylthio, —NR ₆ R ₇ or alkoxy alkyl containing up to 4 carbon atoms, R ₂ is hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl , halogen, nitro, C ₁ -C ₃ alkoxy, , -SO ₂ -NR ₆ R ₇ -SO _N -C ₁ -C ₃ alkyl or -CC- R ₉ and, R ₃ is hydrogen, halogen, C ₁ -C ₃ alkyl, methoxy, methyl and nitro or trifluoromethyl, R ₄ is hydrogen to three halogen atoms, substituted or non-substituted ring is possible C ₁ -C ₄ alkyl , C ₁ -C ₄ cyanoalkyl, C ₃ -C ₆ cycloalkyl, benzyl, -CO-C ₁ -C ₄ alkoxy, -CC-NR ₆ R ₇ or -CO-C ₁ -C ₄ alkyl, R ₅ is hydrogen, nitro, fluorine, chlorine, bromine, methyl, trifluoromethyl, -SO _N -C ₁ -C ₃ -alkyl, -CC-C ₁ -C ₄ alkoxy or C ₁ -C ₃ alkoxy, R ₆ Is hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ cyanoalkyl, mexoxy or ethoxy and R ₇ is hydrogen, C ₁ -C ₆ alkyl or C ₃ -C ₃ alkenyl, or R ₆ And R ₇ attached to nitrogen together to form a saturated heterocyclic ring that forms a 5 or 6 valent ring containing a ring atom or a sulfur atom in the ring, wherein R ₈ is hydrogen C ₁ -C ₆ alkyl, C ₁ -C ₄ Haloalkyl, C ₃ -C ₆ cycloalkyl, C ₄ -C ₇ cycloalkyl or alkoxyalkyl containing up to 4 carbon atoms, R ₉ is C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C _2- C ₆ haloalkoxy, C ₁ -C ₄ cyanoalkoxy alkylthio, C ₁ -C ₆ alkenylthio, C ₃ -C ₆ alkynylthio, C ₃ -C ₆ cycloalkoxy, C ₃ -C ₆ cycloalkylalkoxy , —NR ⁹ R ₇ or alkoxyalkoxy containing up to 6 carbon atoms, W is oxygen or = N-O-R ₁₀ (R ₁₀ is hydrogen, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkenyl N has a value in the range 0-2. If necessary, the sulfonylurea of formula (I) may be converted into a salt of formula (I) by reacting with an amine, an alkylated metal hydroxide or an alkaline earth metal hydroxide, or a quaternary ammonium base. The process of claim 1 wherein Z is oxygen. The process of claim 1 wherein Y is oxygen. The process of claim 1 wherein X is sulfur, —NR ₄ — or —CR ₅ = N—. The process of claim 1, wherein E is —CC = bridged with a methine group. The process according to claim 1, wherein R ₃ is a chlorine, dimethylamino, trifluoromethyl, fluoromethyl, methoxy, ethoxy, difluoromethoxy, methyl or ethyl group. The process of claim 1, wherein R ₃ is hydrogen. The process of claim 1, wherein R ₂ is adjacent to a sulfonyl group. The compound of claim 8, wherein R ₂ is hydrogen, fluorine, chlorine, NO ₂ , C ₁ -C ₃ alkoxy, acetyl -COOCH ₂₂ -CH = CH ₂ , -COOCH ₂ -CH-OCH ₃ -COOCH ₂ C≡CH, The process being —SO ₂ —N (CH ₃ ) ₂ , —SO ₂ —CH ₃ or —CO—C ₁ -C ₄ alkoxy The compound of claim 1, wherein Y and Z are oxygen, E is a methine bridge bond, R ₁ is chlorine dimethylamino, trifluoromethyl, fluoromethyl, methoxy difluoromethoxy, ethoxy, methyl or ethyl group, R ₂ is neighboring a sulfonyl group H, F, Cl, C ₁ -C ₃ alkoxy, _{acetylamino, NO 2, -SO 2 -CH 3} , -COOCH 2 -CH = CH 2 -COOCH 2 -CH-OCH 3, -COOCH ₂ -C≡CH, -SO ₂ -N (CH ₃ ) ₂ or -CO-C ₁ -C ₄ alkoxy, R ₃ is hydrogen. The compound of claim 1, wherein X is a sulfur atom, Y and Z are oxygen, E is a methine bridge, R ₁ is chlorine, dimethylamino, trifluoromethyl, fluoromethyl, methoxy, ethoxy, difluoromethoxy , is methyl or ethyl, R ₂ is the bureau neighboring groups sulfonyl, hydrogen, fluorine, chlorine, C ₁ -C ₃ alkoxy, _{acetyl, -SO 2 -CH 3, NO 2} -COOCH 2 -CH = CH 2 -COOCH ₂ —CH—OCH ₃ , —COOCH ₂ —C≡CH, —SO ₂ —N (CH ₃ ) ₂ or —CO—C ₁ -C ₄ alkoxy and R ₃ is hydrogen. 2. The compound of claim 1, wherein X is sulfur or —CH═N—, Y and Z are oxygen, E is a methine bridge, R ₁ is chlorine, dimethylamino, methoxy, fluoromethyl, methoxy, difluoromethoxy , Methyl or ethyl, R ₂ is adjacent to a sulfonyl group, hydrogen, chlorine, nitro, -COOCH ₂ -CH = CH ₂ , COOCH ₂ C≡CH, -COOCH ₂ -CH-OCH ₃ or -CO-C _1- C ₄ alkoxy and R ₃ is hydrogen. 2. The compound of claim 1 wherein X is —CR ₅ = N—, Y and Z are oxygen, E is a methine defect, R ₁ is chlorine, dimethylamino, trifluoromethyl, fluoromethyl, methoxy, ethoxy, di Fluoromethoxy, methyl or ethyl, R ₂ is adjacent to a sulfonyl group and is hydrogen, fluorine, chlorine, NO ₂ , C ₁ -C ₃ alkoxy, acetyl, -SO ₂ -CH ₃ , -COOCH ₂ -CH = CH ₂ , —COOCH ₂ —CH—OCH ₃ , COOCH ₂ —C≡CH—SO ₂ —N (CH ₃ ) ₂ , —CO—C ₁ -C ₄ Alkoxy and R ₃ is hydrogen. The N- (2-methoxycarbonyl-3-thienylsulfonyl-N '-(4-difluoromethoxy-6-methylpyrimidin-2-yl) urea, N- (4-) Methoxycarbonyl-3-thienylsulfonyl) -N '-(4-difluoromethoxy-6-methylpyrimidin-2-yl) urea, N- (2-chloro-3-pyridinylsulfonyl)- N '-(4-difluoromethoxy-6-methylpyrimidin-2-yl) urea and N- (4-methoxycarbonyl-3-thienylsulfonyl) -N'-(4-difluoromethoxy A method for producing a compound selected from -6-methoxypyrimidin-2-yl) urea and the like. ※ Note: The disclosure is based on the initial application.